25282-60-4Relevant academic research and scientific papers
The influence of hydrate formation on the Clemmensen reduction of pentacyclo [5.4.0.02,6;03,10;05,9]undecane-8,11-dione and pentacyclo[6.4.0.02,7.03,11.06,10]dodecane-9,
Martins,Viljoen,Coetzee,Fourie,Wessels
, p. 9215 - 9224 (1991)
Hydration of pentacyclo [5.4.0.02,6,03,10.05,9]undecane-8,11-dione led to the formation of a mixture of a geminal diol (80%) and a transannular hydrate (20%) and not to only the latter as previously accepted. Compounds with smaller intercarbonylic distances formed only transannular hydrates which promoted rearrangement reactions during Clemmensen reduction. The transannular hydrate of pentacyclo [6.4.0.02,7.03,11.06,10]dodecane-9,12-dione produced pentacyclo [6.4.0.02,6.05,9.04,12]-2-dodecanol.
Reductive Carbon-Carbon Cleavage in Caged Systems. A New General Synthesis of Linearly Fused cis-syn-cis-Triquinanes
Mehta, Goverdhan,Rao, Kotha Sambasiva
, p. 5537 - 5543 (1985)
A concise and flexible approach to cis-syn-cis-tricycloundecane-4,10-dione derivatives bearing the fused tricyclopentanoid framework has been established.The key concept in this synthetic theme is sequential, reductive carbon-carbon bond cleavage in readily and abundantly available pentacycloundecane-8,11-dione (Cookson's dione 7).Reaction of 7 with zinc dust in acetic acid under sonic irradiation resulted in the formation of tetracyclic dione 8 in excellent yield through C 1 -C 7 bond reduction.The second C-C bondreduction (C 9 -C 10 in pentacyclic dione 7) was achieved by treating the tetracyclic dione 8 with an excess of Na-K alloy in the presence of trimethylchlorosilane to give cis-syn-cis-tricycloundecane-4,10-dione (6).Several interesting transformations of the readily available cis-syn-cis-triquinane dione 6 are described.In an analogous manner, methyl-substituted derivatives 21 and 22 of the Cookson's caged dione are transformed to tricyclopentanoids 24 and 26, respectively, in moderate yields.The three hexacyclic diones 29,34, and 35 sharing common structural features with 7 also undergo sequential C-C bond reductions to furnish novel polyquinanes 31,36, and 37, respectively.These examples support the generality and preparative utility of the approach delineated here.
The first cns-active carborane: A novel p2x7 receptor antagonist with antidepressant activity
Wilkinson, Shane M.,Gunosewoyo, Hendra,Barron, Melissa L.,Boucher, Aurelie,McDonnell, Michelle,Turner, Peter,Morrison, Daniel E.,Bennett, Maxwell R.,McGregor, Iain S.,Rendina, Louis M.,Kassiou, Michael
, p. 335 - 339 (2014/06/09)
Relative to other polycyclic frameworks (1-3), a carborane cage (4 and Cs·5) exerts a significant biological effect as an inhibitor of the purinergic P2X7 receptor (P2X7R) which allows one to target depression in vivo and thus demonstrate, for the first time, that a carborane has the capacity to modify CNS activity.
Observations on the samarium diiodide-promoted C-C fragmentation/ring expansion chemistry of some aliphatic 1,4-diketones
Williams, D. Bradley G.,Blann, Kevin,Holzapfel, Cedric W.
, p. 219 - 220 (2007/10/03)
The observations on the samarium diiodide-promoted C-C fragmentation/ring expansion chemistry of some aliphatic 1,4-diketones were presented. It was found that some photochemical electron transfer, as well as SmI2-mediated transformations were carried out on non-aromatic substrates. It was shown that given the otherwise identical molecule, the ability of the SmI2 HMPA complex to chelate the 1,4-dicarbonyl moiety in the one case and not in the other is the primary factor that determines the fragmentation reaction.
The synthesis of 2,3,5,6-endo,endo,endo,endo-tetrakis-substituted bicycloheptanes
Butler, Douglas N.,Munshaw, Timothy J.
, p. 3365 - 3371 (2007/10/02)
Oxidation of the readily available diketone 2 affords high yields of the symmetrical dilactone 5, from which the all-endo tetrakis(hydroxymethyl)norbornane 10 can be made.A related tetrol 22 is also described.These tetrols are dehydrated to polycyclic di-
